I have to say that one thing I really like about the crossfit website is Greg Glassman's dedication to getting information out in his journals. I just thought I would post his recommendation for pushup milestones. I'll also post the link to his pushup article. Very well written. And one hell of a challenge!

10 Push-up Milestones and Challenges
Here is a progression that should keep anyone busy for a couple of years.
1. Fifty honest basic push-ups
2. Ten handstand push-ups
3. 100 honest basic push-ups
4. Fifteen handstand push-ups
5. Tabata interval basic push-ups with 20 reps in each of 8 intervals
6. One handstand push-up without use of wall
7. Ten handstand push-ups without use of wall
8. Fifteen handstand push-ups without use of wall
9. Twenty handstand push-ups without use of wall
10. One handstand push-up without use of wall and on fingertips.

Back in high school, I was on the wrestling team. One day some of the guys on the team got in trouble for talking in practice in spanish. Then they got in trouble for refusing to tell the coach what they'd said. The first problem was our coach believed that if one guy got in trouble, the whole team did the punishment. The second problem was that his punishments usually involved increments of 100 pushups. We ended up doing 400 pushups as punishment for those guys talking.... I can't say that mine were exactly honest pushups (perfect form and all that) but I did every single one of them. Took about 20 minutes as I recall. Those guys didn't last long on the team after that.

I was on the wrestling team back in high school, too. I ended up winning a bet that I could do 300 honest pushups. I ended up doing it AFTER the match in the opponents locker room with both teams watching. I won the bet ...had to or else I would never live down spouting my mouth off!

Back then my main strength workouts were climbing a two story climbing rope. I don't think they let schools have those in the US anymore due to liability.